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Bis ‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations
Author(s) -
Adam Mohamed Shaker S.,
Ahmed Mohamed S. Mohamed,
ElHady Omar M.,
Shaaban Saad
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5573
Subject(s) - chemistry , substituent , catalysis , sulfonate , chelation , medicinal chemistry , ligand (biochemistry) , cyclooctene , schiff base , nuclear chemistry , stereochemistry , polymer chemistry , inorganic chemistry , sodium , organic chemistry , biochemistry , receptor
Two cis ‐ bis ‐dioxomolybdenum oxalylsalicylidenedihydrazone complexes (MoO 2 L1 and MoO 2 L2) were synthesized via the complexation of dioxomolybdenum (VI) acetylacetonate with oxalylsalicylidenedihydrazone (H 2 L1) and p ‐sodium sulfonate oxalylsalicylidenedihydrazone (H 2 L2) bis ‐Schiff base chelating ligands, respectively. The structures of the newly synthesized complexes were confirmed by 1 H‐ and 13 C‐NMR, IR, ultraviolet–visible and mass spectra, as well as elemental analyses (EA) and conductivity measurements. The spectrophotometric continuous variation method revealed the formation of 2: 1 (metal: ligand molar ratios). DFT studies were applied for the ligands and their Mo‐chelates. Interestingly, the bis ‐MoO 2 (VI) oxalyldihydrazone complexes showed remarkable catalytic sufficiency towards the selective (ep)oxidation of 1,2‐cyclooctene, benzyl alcohol and thiophene using H 2 O 2 or tert ‐butyl hydroperoxide ( t BuOOH) at 85 °C. Under aqueous conditions, the MoO 2 L2 (with p ‐sodium sulfonate substituent) exhibited superior that of the MoO 2 L1 (without p ‐NaSO 3 ―group), highlighting the role of sodium sulfonate substituent in the catalytic progress of the Mo‐chelate. The ligands (H 2 L1 and H 2 L2) and their corresponding Mo‐complexes (MoO 2 L1 and MoO 2 L2) were assessed for their antitumor and antimicrobial activities. Furthermore, the antioxidant activity was also evaluated using the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and superoxide dismutase (SOD) assays. The binding nature between the Mo‐complexes and calf thymus DNA (ctDNA) was also studied within spectroscopic and hydrodynamic techniques.